J. Lipid Res.
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
QUICK SEARCH:   [advanced]


     

This Article
Right arrow Full Text (PDF)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Rao, P. V.
Right arrow Articles by Cornwell, D. G.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Rao, P. V.
Right arrow Articles by Cornwell, D. G.
Social Bookmarking
Add to CiteULike   Add to Complore   Add to Connotea   Add to Del.icio.us   Add to Digg   Add to Reddit   Add to Technorati  
What's this?

Journal of Lipid Research, Vol. 8, 380-390, July 1967
Copyright © 1967 by Lipid Research, Inc.

Synthesis of fatty aldehydes and their cyclic acetals (new derivatives for the analysis of plasmalogens)

P. Venkata Rao , S. Ramachandran , and David G. Cornwell

Department of Physiological Chemistry, The Ohio State University, Columbus, Ohio 43210

Saturated and unsaturated fatty aldehydes were prepared in good yield by the reduction of acid chlorides with lithium aluminum tri-t-butoxy hydride. Saturated odd and even numbered aldehydes were prepared by the ozonolysis-reduction of 1-alkenes. Ozonides were hydrogenated with a Lindlar catalyst or reduced with dimethyl sulfide.

Several diols, including 1,3-propanediol and ethylene glycol, were used to synthesize cyclic acetals from aldehydes and plasmalogens in quantitative yield. Cyclic acetals were synthesized from 2,4-dinitrophenyl hydrazones when an exchanger such as acetone or acetylacetone was included in the reaction mixture.

A number of physical and chemical properties indicate that cyclic acetals are stable compounds which do not decompose during storage or gas-liquid chromatographic (GLC) analysis. The cyclic acetals have unusually long retention volumes which are probably related to the large dipole moments found with cyclic compounds. These derivatives are, therefore, readily separated from their aldehyde and methyl ester analogues on polar and nonpolar stationary phases. GLC analysis of the aldehydogenic moieties in plasmologens may be conveniently carried out by direct conversion to cyclic acetals without preliminary isolation of aldehydes or removal of methyl esters by saponification.

Supplementary key words fatty aldehyde • lithium aluminum tri-t-butoxy hydride • Lindlar catalyst • dimethyl sulfide reduction • 2,4-dinitrophenyl hydrazone • cleavage • dimethyl acetal • cyclic acetal • dioxolane • IR spectra • thin-layer chromatography • gas-liquid chromatography • bovine heart • choline and ethanolamine glycerophosphatides

Submitted on February 23, 1967
Accepted on April 19, 1967


Add to CiteULike CiteULike   Add to Complore Complore   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us   Add to Digg Digg   Add to Reddit Reddit   Add to Technorati Technorati    What's this?




HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
 All ASBMB Journals   Journal of Biological Chemistry 
 Molecular and Cellular Proteomics   ASBMB Today 
Copyright © 1967 by the American Society for Biochemistry and Molecular Biology.